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1,2-Dichloroethane → 3'-(4-Fluorophenyl)-4-[3-(1,3,5-trimethyl-1h-pyrazol-4-yl)-propyl]-3,4,5,6-tetrahydro-2h-[1,2']bipyrazine hydrochloride

HRID 220502
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HRID 220502 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1.[CH3:20][N:21]1[C:25]([CH3:26])=[C:24]([CH2:27][CH2:28][CH:29]=O)[C:23]([CH3:31])=[N:22]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:46]CCCl>>[ClH:46].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([N:14]3[CH2:15][CH2:16][N:17]([CH2:29][CH2:28][CH2:27][C:24]4[C:23]([CH3:31])=[N:22][N:21]([CH3:20])[C:25]=4[CH3:26])[CH2:18][CH2:19]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 4

HCID 111,2-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 673669592-(4-Fluorophenyl)-3-(piperazin-1-yl)pyrazineHCID 866416503-(1,3,5-Trimethyl-1H-pyrazol-4-yl)-propionaldehyde

생성물 1

HCID 685957213'-(4-Fluorophenyl)-4-[3-(1,3,5-trimethyl-1h-pyrazol-4-yl)-propyl]-3,4,5,6-tetrahydro-2h-[1,2']bipyrazine hydrochloride수율 78%

실험 절차

Dissolve 3′-(4-fluorophenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.300 g, 1.16 mmol) in DCE (15 mL). Add 3-(1,3,5-trimethyl-1H-pyrazol-4-yl)-propionaldehyde (0.232 g, 1.39 mmol), and stir at room temperature for 10 min. Add sodium triacetoxyborohydride (0.369 g, 1.74 mmol) and stir at room temperature for 18 hr. Purify by SCX chromatography, followed by silica gel chromatography, eluting with 45:45:10 DCM:hexanes:ethanol, to give the free base of the title compound (368 mg, 78%). Dissolve the free base (0.362 g, 0.888 mmol) in methanol and add a solution of ammonium chloride (0.047 g, 0.888 mmol) in a minimal volume of methanol. Shake for 3 hr. at room temperature and concentrate to give the title compound (395 mg, 100%). MS (ES): m/z=409 [M+H]+.

후처리

  1. customPurify by SCX chromatography
  2. washeluting with 45:45:10 DCM

출처 및 근거

ORD 기록
ord-394a4063c8ab4e4ebde7eb93766a17d1
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08202873B2

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